


From bad to Worse

by spankingfemme



Category: Black Sails
Genre: Anal Sex, BDSM, Chastity Device, Cunnilingus, F/M, M/M, Slavery, Spanking
Language: English
Status: Completed
Published: 2014-04-01
Updated: 2015-01-18
Packaged: 2018-01-17 18:26:34
Rating: Teen And Up Audiences
Warnings: Creator Chose Not To Use Archive Warnings, Rape/Non-Con
Chapters: 2
Words: 8,612
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1398028
Author URL: https://archiveofourown.org/users/spankingfemme/pseuds/spankingfemme
Summary: <blockquote class="userstuff">
              <p>Takes place at the end of season 1 where Vane tells Jack that he'll never sail under the black again. Of course what could be worse than being stuck at the brothel? Being stuck at the brothel under the former madam Mrs. Mapleton *evil grin* My plot written by my lovely husband! I am loved! :) WARNING! Contains spanking and non-con M/M! Gritty just like the show, you've been warned!</p>
            </blockquote>





	1. Chapter 1

Jack considered himself to be a very witty person. In fact, Jack would once have boasted that there was nothing anyone could say that could shock or surprise him enough to leave him speechless. Many would have agreed with this notion, too; Jack was after all an absolute master in the art of speech.

Nonetheless, here he found himself without words despite his enormous vocabulary and eloquence. He could only blink and stare at Charles as the other man told him that instead of killing him for the alleged act of treason (which he could unfortunately not invalidate without committing very real treason against his partner Anne) he would instead be left to “rot with the whores”.

Taking Jack’s stunned silence as acceptance of the awful choices left him, Vane smiled, stood, and turned to leave. The former Madam of the house stepped forward, her face positively aglow, “It would seem things have properly asserted themselves”, she said, “I told you that you would regret your boyish actions.”

Jack ignored her, his mind racing over what all of this meant and grasping the true severity of this rather difficult problem. She continued speaking, perhaps assuming that he cared what she had to say, “I believe even you understand that I will be returning to my previous station as head mistress of this house.”

That got Jack’s attention; as he looked over to her, she made a grand dismissive gesture, “As I am of course in charge, my first action is going to be to terminate your employment.” She hesitated before imitating his previous sarcasm, “Thank you very much.”

Jack finally returned to his senses, realizing that he was heading into a death trap, “Madam, we are both aware that if I leave this place that man will kill me. As this is the case, I will still need a means of gainful employment…” Jack paused; he had never been a prideful man, but giving her this still stung, “perhaps we can come to an arrangement?”

She chortled, fanning herself with the little paper fan she always carried with her. The uncomfortable (at least for Jack) silence hung in the air for some few moments before she finally replied in a fashion that made it clear she wished him to suffer a while longer, “I’ll think about it. Why don’t you… hang around until I make up my mind?”

She laughed at Jack’s helpless expression, and finally turned to head upstairs to the small office that Jack had until recently called his own, “I need to get my house in order, now that we are clear on who really runs this place.”

Jack let out a lot sigh, realizing he had been holding his breath for a really long time. He glanced up at Anne, who shared his look of worry. Vane had not threatened her specifically, but they both knew without asking that her fate was intertwined with his.

Hell, Charles Vane might even have deduced that the entire betrayal was actually her idea all along, and that she had strong-armed Jack into it. Their antics were, after all, not entirely unknown among their former crew.

Jack took another look at Anne, and saw that she knew what he was thinking as she moved to take a seat at the bar; all that was left now was the waiting.

She made them wait for several days. Anne told Jack that she wished to give the bitch a piece of her mind, but Jack stoically advised her that as Vane technically owned the whore-house, threatening the currently re-instated Madam would prove pointless as they could not back up such hostility.

At last though, Mrs. Mapleton finally deigned to speak to Jack further on the matter, apparently having decided that she had seen him squirm long enough. “You’ll be a chore-boy, and Anne will be a bouncer.”

Jack licked his lips, knowing that his inferior title was most likely non-negotiable (because it was obviously another in a long list of punishments bound to come) but figuring it wouldn’t hurt to try, “You know, I have spent some amount of time under the black flag; I assure you that I could likewise make a fearsome guardian for this fine establishment.”

Mrs. Mapleton smiled and patted his cheek, “Oh you couldn’t scare a fly, my dear. No, I think you are far better served in a more… menial position.”

Jack nodded, having entirely expected this reaction, but finding himself with little choice in the matter. At least she hadn’t tried to have Anne become a whore; that would almost certainly have ended in disaster. “Very well… Madam, it will be as you say.”

The mistress of the house only smiled at his obviously begrudging tone, and waved her hand at him, “You shall begin work at once; see to it that those table over there are bussed and that my girls don’t need anything.”

Jack nodded and moved to tell Anne about the new development on his way to the indicated tables, when Mrs. Mapleton called out to him once more, her voice filled with wry amusement, “Oh, and Jack… I’ll be checking in on you occasionally; I don’t think I need to remind you how much incentive you have to be diligent in your duties…”

Jack only nodded again, deciding then that he now thoroughly hated this woman. Jack wasn’t prone to hate; usually stupid people or people who tried to push him around only annoyed him, but no, no this woman he hated with all of his heart.

She would be ousted again, of that he promised himself. It would just take time and a plan, so he would play along with her insulting schemes for the time being, and grant himself the reprieve needed to think.

So it was that Jack Rackham, former quartermaster under the profitable Charles Vane was now a lowly servant to a whore-house Madam, cleaning tables, serving drinks to drunken sailors and scrubbing vomit off the baseboards.

This went on for several days and though Jack tried hard to find a way out of the particular mess he was in, he found himself rebuffed at all corners. Max had been demoted back to whore (the only reason Mrs. Mapleton had not thrown her into the streets being her fear of Mrs. Guthrie) and despite Jack’s insistent pleas to repay his kindness by seeking aid from Mrs. Guthrie she repeatedly turned him down. Apparently she would rather die than ask for help from Eleanor.

Anne was less than helpful, becoming entirely too comfortable in her new position as hired thug for the house, especially since Mrs. Mapleton actually paid her well. Jack was surprised at first but quickly realized that the old crone was only separating him further from his allies.

He realized the strategy was working when after he consulted Anne on how they might remedy the new situation she told him, “Give it up, Jack; she has you by the balls… besides, I think your new position rather suits you. Maybe if you do well enough she’ll promote you to advisor or something, since you aren’t good at much else.”

Jack did his best to hide his offense, knowing that Anne only got off on it, and tried his luck with a variety of other deckhands whom he knew little or nothing about. They all laughed him away, though. Tale of how he had ‘betrayed’ his crew had spread like the plague, just as Vane had promised it would, and he couldn’t even get anyone to hear him through an entire sentence.

This only left him with the least capable to fall back on, which he didn’t bother with; after all, if he put his faith in the dumbest swindlers in Nassau, he’s just end up dead for his efforts. Occasionally as he made these rounds he would catch the Madam watching him, and from the small smile she always wore, he could tell that not only did she know what he was ‘secretly’ doing, she thought it amusing.

Just keep smiling you old whore; thought Jack, no one holds all the cards all the time, and one day you’ll see who you’re messing with.

Weeks passed him by and Jack’s frustration grew as he watched the Madam take measures to circumvent his departure from his current circumstances. Even should he become desperate enough to try to flee the island entirely, she had, according to those that would speak to him of it, set quite a few eyes watching for him with promise of reward should they return her ‘wayward servant’ to her.

Additionally she blocked him even from making money at gambling by forbidding her patrons to play him at cards or any other form of monetary risk. Considering the gravely low wages she afforded him for his chores Jack did not see himself ever obtaining the necessary funds to properly bribe his way out of the brothel.

Force certainly wasn’t an option, either; Jack had never really been the best fighter, and he had a feeling he would be grossly outnumbered immediately upon his exit of the house. He mulled over the idea of assassination constantly, but Jack knew he would be the first and probably only suspect in such a murder as soon as Mrs. Mapleton was discovered dead.

He could try framing another girl for the act, but that wouldn’t remove him as a suspect, and people were well aware of his prowess in manipulation; the incident would be investigated thoroughly, and the slightest slipup would mean the end of him.

Besides, he thought with a sigh, framing people for murder really wasn’t his cup of tea, and despite how hard he might occasionally tell himself he was, he knew all of the girls here now; having their death on his conscience might bother him a little.

For the next week Jack drowned his sorrows in extremely cheap alcohol and the sweet embrace of Anne’s arms, at least when she allowed him to hold her and didn’t insist on tying him up. For it had become painfully clear to Jack that his options weren’t really options at all; he simply had a list of unpleasant choices to choose from.

Despite how much distaste he had for continuing on as the errand-boy for the devil’s own Mrs. Mapleton, he had to swallow whatever still remained of his pride and bite this ignoble bullet. Brainstorm as he might, when the thunderheads of his thoughts had cleared, he was still just as damnably stuck waiting for something to happen that might change the nature of his situation.

So it was that a full month passed by, and despite his inordinate amount of ass-kissing, the Madam was not only unimpressed, but she seemed to always think he wasn’t suffering enough. She routinely gave him the most vile, degrading tasks she could think of and he would swear that she was perhaps dissatisfied that he did them so readily.

Jack suspected that she would have liked him to groan and moan concerning her orders to clean the latrine, and as he watched her reactions further it became clear to him that she actually just wanted him unhappy.

Accordingly, Jack spent all of his time thereafter moping about and wearing his feelings about where he now stood on the outside. Sure enough, Mrs. Mapleton was amused in short order. Jack sighed when he observed her up on the balcony tittering happily with the girls as she watched him mopping the floor in a dejected fashion.

Unfortunately, knowing what Mrs. Mapleton wanted did him no good; how do you barter with someone who just wants to see you miserable? Jack thought on it for a while and decided he had only one real option, and it was certainly a stretch; he would have to act as depressed as possible until the old bag finally got tired of him to the point of forgiving him their earlier rivalry.

Jack didn’t much care for an action like this one, of course; he wasn’t actually a gambling man, when he played cards he usually cheated. Doing something that wasn’t a sure thing went against his nature, but for lack of any better ideas or promise of any to come, Jack resigned himself to the abysmal notion of ‘hope’.

Jack raised a dirty glass of cheap swill in toast to his own inner thoughts, “Here’s to finding out just how unlucky I am.”

The answer came to Jack a few days later; a large brute of a man walked up to him and, quite unexpectedly, grabbed a firm hold of Jack’s crotch. Jack squeaked a little, such was his surprise, and he requested an explanation in a voice a timber higher than usual, “Sir, you seem to have misplaced your hand.”

The huge bald fellow only smiled, and Jack realized at once that the man was missing many of his teeth and that the odor of his breath was most foul. Jack recoiled as much as the firm grip on his genitals allowed, trying a different approach, “I see… well, sorry to inform you of this my good man but I’m just a waiter here; I’m not up for sale and I certainly prefer the fairer sex.”

“Belay that.” Mrs. Mapleton approached from across the way, “As I informed this man only moments ago, you are indeed a member of this brothel, and if he’s willing to pay for a bite of the forbidden fruit, I am loathe to turn him down.”

Jack squirmed, gently taking the other man’s hand and guiding it away from his gender; thankfully, his grip released and Jack could breathe again. “Would you be so kind as to allow me a word with the Madam concerning our contract?”

The brutish man frowned but didn’t move to interject when Jack receded to talk closely to Mrs. Mapleton, whispering, “I’m sorry if I failed to inform, mistress, but I have only ever been in the company of women and would made an exceedingly poor whore.”

Mrs. Mapleton smiled, sharing his conspiratorial lowered voice, “That’s quite all right, my dear; I’m sure with a little practice you will get the hang of it. After all, you have very fair features; the kind of softness often lusted after by men like these.”

Jack’s eyebrow twitched and he steepled his hands together, touching his index fingers to his lips before continuing, “All right, I get it; you still want me to pay further for past damages. I understand, and I will happily continue to make it up to you in other ways, but not like this, you must understand; I simply have no interest in men.”

The mirth left the Madam’s face and her voice was low and menacing, “I couldn’t give two shits what you want, and you aren’t the one who decides how pay for your hubris, I am. You’re going to go with this man and suck his prick or allow him to shove himself into your ass and you’re going to do it because I told you to.”

Jack hated where this was going, knew where this was going, but found himself having to play it out anyways, “And if I should refuse?”

Mrs. Mapleton’s smile returned, only it was cruel and without mirth, “Then you will find yourself thrown out of my house, out there on the streets where we both know you won’t live to see morning.”

Jack ran a hand through his hair, pacing a little before returning to continue the fierce whispered conversation, “You don’t know that; I might just make it off of this fucking island; what’s more do you really want to risk losing the chance to continue torturing me daily over this?”

The mistress shook her head, still smiling, “I know you have been snooping, and in case your busy bees didn’t tell you, I have warned Vane’s men that you might try to bolt today; you haven’t a snowballs chance in hell of survival. Besides, we both know you’re a coward.”

Jack took offense but decided that showing it would only please the matron further. So instead he chose the path of least resistance, since she was right; he couldn’t defy her now, not like this. “Very well, I shall see this… gentleman to my room immediately.”

Mrs. Mapleton looked surprised and Jack realized she has expected him to whine or complain quite a bit more. It gave him some satisfaction to know that she had just realized he wasn’t as predictable as she had apparently foreseen.

He would be sure to continue to surprise her in the immediate future, because he’d be damned if he was going to literally be taking this lying down. She only waved in obviously feigned indifference, “Go on, then, make me some money, whore.”

Jack approached the hairy man off to the side and smiled, “Would you mind if we went somewhere more private to have a chat?”

The burly man smiled in an overt display of sexual avarice, and he clamped a hand on Jack’s ass as they strode around the corner and into the small hallway that led to Jack’s room at the far end (he of course had the worst accommodations possible thanks to Mrs. Mapleton, only one step up from a broom closet).

The Madam, for her part, smiled as she watched the two of them round the corner, and seeming to be satisfied with what she saw, she moved on to attend to other business. Jack glanced over his shoulder and waited until they were down the hall a ways before talking to the beefy sailor in hushed tones, “There has been a reason that I haven’t been sleeping with anyone despite my occupancy in a house of pleasure…”

The boorish man looked confused, “…What?”

Jack started over, speaking slowly, “I haven’t been fucking the women here, or any men for that matter…” he gave the man a conspiratorial look before leaning in to whisper very softly, “I’ve got the cock rot.”

The other man made a face of disgust and backed away a few paces. Jack went on, “The Madam only now found out, and I’m sure you can understand why I don’t want to go public with such shaming news; I will likely be dead by this time next month and my name is all I have left, tarnished as it already is…”

The sailor only nodded, his face still twisted into a look of distaste. Jack smiled, “The Madam may continue to solicit me as a genuine whore to gentlemen of your… tastes, but only because she is so kind-natured and doesn’t want everyone knowing about my condition. If I could ask you a favor, could you kindly tell those you know who might be interested in me the truth so as to avoid further confusion?”

The man nodded, and then walked away quickly, as if merely standing next to Jack might cause his member to shrivel up. Jack smiled; heading into his room to open the musty bottle that contained what was left of the disgusting watered-down liquor he had stored there. He toasted himself, “Another satisfied customer, Jack.”

A number of weeks passed, and the discussion Jack knew was coming finally arrived; the Madam asked him to accompany her to her small office upstairs. Jack had expected this talk was due, but he had to admit he was surprised with the secrecy; Mrs. Mapleton never used her office.

Jack realized as they entered that the use of the small room might have been partly to veil a surprise for Jack; the burly fellow he had lied to weeks ago stood within, his arms crossed over his chest and staring at Jack in a manner most surly.

Jack had learned after that day that the man’s name was Pits, or at least that was what the other members of his crew called him, for no right-thinking father would ever name his child Pits. Jack gave him a friendly smile, “Hello there, old friend.”

Mrs. Mapleton raised an eyebrow and shut the door behind them. She folded her hands neatly in front of herself and addressed Mr. Pits, “Sir, I have brought my whore here to clarify the awful rumors he has spread due to a capricious nature left unchecked.”

Jack fidgeted but didn’t say anything as Pits continued to glare at him. Finally the bear of a man spoke, “You lied to me?”

Jack cleared his throat, weighing his options as Mrs. Mapleton needled him with her own intense gaze from the side. He had been found out as he had known he would, but he hadn’t expected the Madam to involve the man that he had initially lied to.

He had planned on lying further to set the old hag awry for at least a while longer, but clearly she was not only unwilling to allow him the opportunity, she intended to bring things to a head immediately with the bitter irony of the whole ‘dishonest whore’ bit.

At last he licked his dry lips and spoke, “I admit it was a story in poor taste, by my matron here simply will not accept that I am uninterested in men; I am in the awkward position of trying to make her happy while maintaining the chastity of my asshole… surely you can understand I meant no real harm?”

His fast-talking seemed to have had effect by the look of confusion on Mr. Pits’ face, but Mrs. Mapleton stepped in the rain on his parade as she was prone to do, “In other words, this whore fails to understand that the Madam of the house calls the shots, and that he should spread his legs and do what he is told…”

Jack couldn’t help but ruffle indignantly a bit at that last part, and Mrs. Mapleton smiled, ever enjoying his discomfort, “…he will be punished and then offered to you free of charge as apology for the obvious lack of discipline.”

Jack’s eyebrows shot up, “Punished? Whatever did you have in mi…? Oh.” Jack swallowed as Mrs. Mapleton opened a cabinet on the other side of the room which contained a large assortment of paddles, switches, straps and even a few cat-o-nine-tails.

These were obviously devices held for the use of more eccentric guests to the whore-house, but clearly Mrs. Mapleton was not averse to putting them to other uses. She reached up, plucking a thick leather strap from a nail on the closet door.

She turned, taking a few steps forward and smiling when Jack took a few steps back, “Mr. Pits, if you could kindly block the door; I doubt he is stupid enough to run from me, but I’d do him the favor of removing the possibility.”

The huge bald man smiled and moved to the indicated location, folding his arms over his chest again, presenting a very intimidating and immovable-looking blockade.

Jack felt cornered, and the implications of what she planned careened through his mind; he was already seen in a poor light by those that resided on the island, if word of his predicament with Mrs. Mapleton got out, any chance of him sailing under the black would be forever ruined.

“Madam, you aren’t thinking this through; if you persist in your current line of action, it is going to have to become irrevocably clear to Mr. Pits that I am not never ever was a whore employed by you.” Jack moved to put the small desk at the back of the room between him and the elderly woman as she advanced.

Mrs. Mapleton chuckled, “Quite the opposite; I intend to make it painfully clear to you that you are mine, as you are the only deluded person in this house who fails to understand his place.”

Jack lost his composure as she circled the desk, chasing him in a circle to avoid her, “You are mad if you think I will allow you to treat me like this; you force a lion into a corner, Mrs. Mapleton. Be aware that anything that happens from here is on you!”

She scoffed again, not relenting in her pursuit as she replied, “You strike me and you die here, boy; in fact, if you don’t start being compliant very soon I will have you thrown onto the street just to enjoy watching how far down the street you can make it from my balcony.”

Jack hadn’t wanted to play his ace yet, but he was out of options, “Anne would never throw me out!”

Mrs. Mapleton smiled, “Perhaps, but look me in the eyes and tell me that she won’t stand aside while I have Mr. Pits here toss you to the dogs.”

Jack froze, unable to contradict her fully; he’d love to say that Anne would step in to defend him, but Mrs. Mapleton had been paying her handsomely for a while now, and Jack had always known his fondness of her wasn’t necessarily reciprocated.

Mr. Pits apparently decided that their ridiculous dance around the desk was fated to end then, for he took Jack’s moment of indecision to lunge forward and grab him, slamming him down into the table, “Stop talking back to the Madam, whore, and do what you’re told. My cock’s gone soft for all this waiting and I intend to be in you soon.”

Jack’s eyes were wide as he contemplated the multiple threats of both Mr. Pits’ promise as well as Mrs. Mapleton’s, helpless to stop her from reaching him now that he was firmly secured to the desk by Mr. Pits’ bulging arms.

To his dismay, Mrs. Mapleton pulled his pants down to his ankles, leaving the stark white nakedness of his buttocks plain to see. She leaned in before getting started, though, “Are we clear on where we stand yet, Jack?”

Jack didn’t answer, once again rendered speechless by yet another situation that offered no real options except ugly endings and uncomfortable ends (this time quite literally).

Mrs. Mapleton seemed to take his quiet for subjugation and put a hand on Mr. Pits’ arm, “Why don’t you stand by the door again, honey; I think our whore is finally starting to get it.”

Pits grunted and did as asked; seeming bored with the interaction and impatient to begin the parts of the encounter that Jack was dreading the most. Nonetheless he waited as patiently as one of his temperament could, staring at Jack’s back-side in a manner that left Jack decidedly uncomfortable.

Jack remained on the desk, knowing that running wouldn’t help him and finally admitting to himself that he was scared; terrified, actually, of what Mrs. Mapleton would do to him should he continue to resist the awful things she had planned for him.

She was apparently more cruel and sadistic than he had predicted before, and though he couldn’t immediately imagine how the situation he was in could get worse, he suddenly found himself without doubt that she could.

The Madam held herself in a manner that suggested she knew he had gone spineless, and her tone spoke that she had in fact been anticipating this exact moment of epiphany, “Poor, poor Jack, thought he was so god-damned clever. Thought that if he waited me out, I’d slip up, and he’d get another go at me.”

The strap flashed down unexpectedly, and Jack gripped the sides of the desk, crying out in pain. Mrs. Mapleton went on, “A whore house is a training ground for dealing with conniving fucks like you, Jack, and I certainly didn’t become Madam of this establishment by being lucky.”

Another swat and Jack writhed on the desk, gritting his teeth and moaning at the extreme discomfort those wicked red welts on his posterior now caused. Worse, Pits was licking his lips in an unsavory way as Jack wiggled about, making the former sailor even more stressed.

Mrs. Mapleton seemed yet to be finished both with his punishment or her lecture, as her voice droned on, “You are a whore now, Jack; because it’s the lowest thing I can feasibly make you into and still curry a profit. But…”

Another stinging swat and Jack called out loudly, unable to check his voice against the searing pain that erupted from being struck in the same tender area twice. He was all too aware that loud yells would undoubtedly be heard from the main lobby outside of the office.

He knew that there would have been those that took notice of him entering the room with Mrs. Mapleton, and even if not, he would certainly be seen exiting after such a loud spectacle. Even the dumbest of Nassau’s pub-crawlers would likely deduce what had happened to him.

The thought of what was going to happen to the shambles of his once-great reputation stung almost as much as the next swat Mrs. Mapleton delivered, which to his great shame caused him to cry out in a high-pitched and perhaps even lady-like fashion.

Unable to bear another seething attack Jack finally retreated from the desk, his hands going to his bottom as he begged mercy, “Please, I…”

Surprise registered again on his face as Mr. Pits hefted him up from behind and placed him back on the desk, “Don’t be such a bitch about it; take your beating as if you were actually a man.”

Stunned by the vulgar but well-timed insult by Mr. Pits, Jack didn’t move as Mrs. Mapleton swatted him again, “He can’t help himself; he has always been weak. We’ll give him a few more to remember that by, and I’m sure he won’t soon forget himself again.”

Jack wriggled under the muscular man’s grip but Mr. Pits was far stronger; a not-so-promising glimpse of what was to come once this preliminary torture finally ceased. Mrs. Mapleton, for her part, gave him the promised few swings of remembrance and then leaned in to smile at him as he panted on the desk, “I told you that you would regret it.”

She hung the strap back on its nail on the closet door and then shut it, still smiling. Giving him one last pointed look, she turned and simply walked out then, pulling the door shut behind her. As the door closed, Jack became uniquely aware of Pits’ hot, heavy breath behind him.

His pants were still down, and from the expression on the sailor’s face, the entire painful episode had actually excited the man. This did not bode well for Jack, of course, and with diplomacy now out of the window thanks to Mrs. Mapleton’s maneuvering, his options were now looking long, hard and painful as Pits pulled his own pants down.

Stalling for time because that was the only thing left to him even if it only prolonged his agony, Jack gave him a weak smile, “May I at least remove myself from the desk?”

Pits shook his head, smiling, “I kind of like it like this, and you are all trussed up here ready and all, no reason not to get right to business.”

Jack grimaced, finally allowing the despair he had been fighting for so long to take a firm grip of him; he couldn’t lie to himself anymore. He had been, was, and for the foreseeable future would always be… screwed.

 

 

 

 

 

 

 

 


	2. Changing Hands

Jack sat in Madam Mapleton’s office, squirming in the comfortable chair in front of her desk. The reason for his unease was directly related to the Madam’s recent streak of cruel and sometimes unusual punishments. She had yet to relax from her efforts to make his life miserable, so a trip to her office could never bode well.

In time Mrs. Mapleton arrived, smiling at him as she sat down behind her large mahogany desk. Jack licked his lips, “Madam… always a pleasure. Whatever can I help you with?”

Mapleton smiled again, seeming to enjoy his unease, “You just sit tight; we’ll be having company in a moment here.”

Jack’s mind raced; who would need to see him and Mrs. Mapleton? His gut sank as he thought it might be Captain Vain; if the vengeful man came by to gloat he may learn of all the… things that the Madam had seen done to him…

But Vain wasn’t who entered the office then; instead, the figure of Lady Eleanor Guthrie stood in the doorway looking Jack over before she entered to be seated across from Madam Mapleton. Jack felt confused but remained quiet, curious about the unexpected visit.

Miss Guthrie opened conversation, looking to Mrs. Mapleton, “I assume you got my message concerning my interest in your… property.”

The Madam smiled, nodding, “Indeed, Miss Guthrie, but if you have heard much about him, then I’m sure you know that Jack is of sentimental value to me, besides being a great earner.”

Eleanor gave a tight smile, “Just tell me how much; I’m sure you know I can afford it.”

As the two women haggled a sale price for Jack, he stood in slack-jawed awe of the sudden twist of events, his heart soaring with the prospect of release from his hellish imprisonment. Miss Guthrie, for whatever reason, had come to save him!

Perhaps Max had changed her mind and decided to help him after all. Bonnie may have convinced her to put in for a favor from her ex-lover, since Bonnie and Max seemed to be getting ever closer these days. But however it happened; it was a day of joy!  


Jack did his best not to smile, lest he give Mrs. Mapleton cause to keep him, since the spiteful old bitch would be ruffled to see him less miserable. Price decided, they stood, Mapleton shaking Guthrie’s hand and nodding toward Jack, “He can be a handful at times, I’ll warn you…”

She walked across the room to a cabinet that Jack had come to know as the storage-place for items of unnecessary violence. From here she removed one of the straps she had punished him with early in his tenure.

She handed the leather strip to Eleanor, “…But if you are firm with him, he’ll straighten out just fine; see how compliant I have made him.”

Eleanor raised an eyebrow at this and took the implement. “Come along, Jack.”

Jack wasted no time, and now that the deal had been struck, he didn’t bother hiding his smile of relief anymore. He expected his optimism to annoy Mrs. Mapleton, but instead of a frown, she only gave him a sly smile back, which in turn caused him to frown again. What did the old cunt know that he didn’t?

Despite the cloud that the Madam had placed over his rescue, Jack managed to find his elation again quickly enough as he was escorted from the Brothel to Eleanor’s own offices. As they walked, he took in a deep breath, smiling, “Ah, freedom. I owe you a debt of gratitude, Miss Guthrie, but for now, I think I need to go get a drink…”

Eleanor turned to face him, “That would be a mistake, Jack. Once Vain learns that I’ve… acquired you, you won’t be safe anywhere but my compound.” On seeing his face fall, she went on, “And like you said; you owe me now, and I intend to see how you can be of use to me.”

She turned, heading up the steps to the second floor, and Jack frowned as he contemplated how he had traded one gilded cage for another. Well, he thought, this cage seemed a hell of a lot better than the last one.

________________________________

 

Jack spent the next several days standing around Miss Guthrie’s office, feeling mostly like an unneeded paperweight. A few times he was able to help her concerning business plans, but Eleanor was a shrewd person in this field, and rarely needed help.

So he spent most of his time with the ultimately mundane tasks of sweeping the second floor office and filing paperwork, along with an assortment of other flavorless activities when he wasn’t simply doing nothing at all.

With all of the excess time, it was easy for him to notice that Eleanor spent quite a bit of time staring out of her window at the balcony across the way, where Max often retreated from the brothel for fresh air. Finally one day he approached her while she was glancing so, and spoke on the matter, “You should go see her.”

Eleanor whipped around, glaring at him so fiercely that he took a step backwards, “She won’t have me; I’ve tried. I can never have her, and it is at least partly your fault! “

Jack stammered, finding himself caught unawares at the sudden anger he found himself under, “I-I swear I never meant to come between the two of you, and I apologize profusely for any involvement of mine that might have led to this!”

Eleanor stalked over to him, glaring at him still as she growled, “Is it true that you and Bonnie are together?”

Jack raised an eyebrow, confused and not entirely sure how much of his… complicated relationship with Bonnie he would want to reveal, “Well… we have fucked… why does she have anything to do with this?”

“She is as guilty as you are for everything that led to me losing her, and I intend to make you both realize that you don’t cross me. I can see by your face that you care for her, so I think I know exactly what to do; I’m going to let you go be with her.”

Jack’s brow furrowed, “I’m afraid I don’t understand…”

Guthrie moved to her desk and opened a drawer, pulling something heavy and metal out to set it on down with a thud. “You’re going to be wearing this. Be sure to let your lover know that I have the key.”

Jack had to look it over a moment before he realized it for what it was; a chastity belt, complete with an intricate lock to prevent anyone opening it that didn’t have the key. “Oh. Are you sure you can’t just let us make it up to you some other way?”

Eleanor shook her head, still glaring, “You two will be denied from being lovers, just as you denied me. Now put it on, and go see her.”

Jack let out a long sigh as he picked up the device, looking it over and wondering how he was going to get out of this one. “I understand you are upset, Miss Guthrie, but you can honestly expect…”

His sentence trailed off when he looked up and saw that Eleanor had retrieved the strap that Mapleton had given her. “I paid far too much gold for you to simply tell me no. I know what the Madam did to keep you in check, too; don’t think I won’t.”

Jack gulped, frozen in place by the unexpected threat, “But…”

“Now!” she yelled.

Jack began putting the girdle on quickly. As embarrassing as wearing it could be, he could tell by the look in Eleanor’s eyes that things could get far more humiliating if he didn’t comply…

 

\--------------

 

“Take off your pants.”

Jack hesitated, and Bonnie shot him a suspicious look, “What, you with Guthrie now, you won’t do what your told anymore?”

She strode across the room and yanked his pants down, despite Jack’s feeble protest, “Wait…!”

Bonnie’s eyes went wide, “What the fuck?! What is this?”

Jack explained what Guthrie had told him, and Bonnie laughed into his face. “If that cunt wants to play this game, she sure as hell shouldn’t have picked you.” She grabbed him by the collar, yanking him down so that he was on his knees, “I can find other ways for you to get me off…”

Jack licked his lips, unable to hide his arousal at the way she pushed him around. He had always relished how Bonnie took charge, loved her for it in fact, though he doubted his love was reciprocated. “Yes, she seems to have forgotten that favors extend beyond the hips…”

Bonnie smiled, closing her eyes, “Now shut up and put your mouth to better use.”

 

\----------------------------------

 

Jack returned a bit ruffled, and Guthrie surprised him by drawing close, sniffing him, “You smell of sex; did that bitch pick the lock or something?”

Jack shook his head, a little surprised that she had been able to smell what they had done. He made a mental note to bathe before returning in the future, assuming Guthrie let him go back at all. “No, ma’am, you can inspect it if you like; it hasn’t been tampered with.”

Guthrie glared, realization dawning on her features, “You fucked her with your mouth.”

Jack jumped with guilt, “W-well, you never said specifically that I couldn’t please her orally…”

She slapped him, and Jack stared down at the floor as she screamed her anger, and then all of a sudden she grew calm again, walking over to sit at her desk, “Get out.”

Jack looked over her way, and noting that she wouldn’t even look at him as she busied herself with her work, he quietly left the room to retreat to the servant’s quarters where he slept.

 

\--------------------------------------------

 

The next morning Jack went to Guthrie’s office early, planning to apologize for his failing and ask forgiveness; after all, Eleanor had still saved him from a fate perhaps worse than death, and he thought he might get out of putting the chafing chastity belt back on if he could curry a bit of favor.

Jack wandered from the office to her private chambers when he saw that she wasn’t waiting for him as she usually was, and knocked lightly on her door, “Milady, are you up?”

The door opened and Jack gazed upon Eleanor in her nightgown, looking disheveled with a glow about her that he couldn’t place. The way she looked at him made him uneasy and he looked away, “I apologize, Miss Guthrie, I…”

She surprised him, grabbing hold of his collar and yanking him into her bedroom. Jack yelped as she reached down and took hold of his member, squeezing as she told him huskily, “I thought of a way you could repay me. After all, I do own you…”

Jack was almost eagerly compliant as she ripped his pants off of him and pushed him back to her bed. She wasted no time for foreplay, having apparently already been warmed up; she threw her leg over him, taking only a moment to line his cock up with her hand before shoving herself down on him.

Jack gasped as she began thrusting and gyrating upon him, and he reached up to take her breast in hand, thinking to give her a kiss, but she put both hands on his chest and shoved him back down onto the bed. “No. You are here to please me.”

This only made Jack harder. She couldn’t know that such treatment aroused him, could she? As she pulsed up and down on his dick he tensed, feeling close to release. She seemed to sense this and stopped, glaring at him, “You had best not cum until I say so; I’m not there yet.”

Jack gulped, nodding even as he spoke negatively, “I want to, but I don’t know if I can hold it… I’ve been in a chastity belt during sex recently and…”

Guthrie gave him a humorless smile, “If you don’t do as you’re told, I’m going to go get the strap.”

This was the encouragement he needed, and Jack nodded again his assent. Guthrie took a long moment to just look at him, and Jack had the distinct impression that she was reading him like an open book. Never in his life had he felt so exposed.

Then she drove down on him again, thrusting herself hard on him until sweat beaded on her tensing thighs and across her breasts as they bounced to the rhythm of her fucking. Jack bit his lip, using all of his will to suppress the desire for release.

Finally, she tensed up, her legs squeezing him hard as her body shuddered in the throes of orgasm. She squinted her eyes closed and undulated a long cry as the waves of pleasure cascaded over her. She collapsed on his chest, and Jack could feel her heart hammering as she took fast, deep breaths.

After a while, Eleanor lifted her head, giving him a small smile as she pulled free of his cock, “Maybe I should have invested in a personal toy before now; that was fun.”  She glanced down and then returned her gaze to his eyes, studying him. “You didn’t get off, poor thing.”

She reached down, taking his member in her hand and rubbing it gently, causing Jack to stir involuntarily. “Don’t worry; I’ll take care of you.” She jerked him slowly at first, increasing tempo as his breathing quickened until she was beating him off hard.

Jack screamed out loudly as he ejaculated, Eleanor still pumping his penis in her palm as he shuddered in ecstasy. Eleanor leaned in to whisper almost conspiratorially, “I bet Bonnie isn’t going to enjoy the fact that you’ve been fucking around, Jack.”

Jack shot her a look, “Wait… this wasn’t all contrived just to make my… partner jealous…?”

Guthrie simply gave him a look and rose from the bed, “You can go, now. Put your belt back on and go see your lover again.”

Jack was stunned. He was caught between two women’s quarrels and it had just gotten him laid. He wasn’t sure how to feel about that. He moved numbly back into the office and retrieved the chastity belt, and Eleanor followed soon after to make sure it was locked tightly.

She smiled and gave him a light smack on the ass as she went back to her quarters, “Be sure to tell me exactly how it went.”

 

\---------------------------------

 

When Jack returned a few hours later Guthrie took him back to her office alone, unlocking his girdle and taking a deep breath over him, frowning, “You still smell like sex.”

Jack recoiled; this time he had bathed… how did she manage to pick up on that? Eleanor frowned, “I can smell her tang on your breath. She doesn’t care at all that she can’t have your cock does she? So… did you tell her that I fucked you?”

Jack piped up immediately, “Of course… she, uh, just wasn’t concerned, I suppose. After all, I am in the custom of bedding multiple women at a time, and it has never bothered her in the past. She has no reason to hate you, you know…”

Finally Jack felt like he might have found a way out of the situation with the chastity belt. If he played his cards right, he could perhaps be with both women, as well. He allowed himself a smile when he thought she wasn’t looking.

That smile withered as Guthrie pulled a familiar item from her desk. She allowed one end of the strap to repeatedly smack her other hand as she approached him again. “I don’t like being lied to, Jack.”

Jack tensed, “I wouldn’t dream of it… I told her just as you asked…”

Eleanor raised an eyebrow at him, “Oh, is that what you were lying about? Well, that is direct disobedience, Jack. We’re going to have to address that… go to my room… now.”

Jack was going to object again, but her threatening advance drove him to retreat in the described direction, so he moved there, his mind awhirl on how he could avoid this new problem. He had in fact not been able to tell Bonnie about having lain with Eleanor; she would have killed him!

Jack sought fast to assuage Eleanor’s suspicions, “Milady, I assure you…”

Guthrie didn’t seem to be interested in what he had to say, shoving him as she had previously so that he once more lay upon the bed, except that this time she remained clothed and did not join him. She simply said, “Turn over and pull your trousers down.”

Jack stared up at her a moment in disbelief, unable to believe that this was happening at all. Memories of his time under Madam Mapleton’s care caused his butt-cheeks to clench in anticipation. “Miss Guthrie, please, let me explain myself.”

Eleanor shook her head, “No. No more silvered words, no more diplomacy from your conniving tongue. Just do what I tell you to and remember who you work for. Do you want to go back to Mrs. Mapleton?”

Jack thought on his options a moment and then reluctantly pulled his trousers down, even more reluctantly turning onto his stomach. “Alright, I… Ahh!”

His words were cut short as Eleanor began swatting him immediately and earnestly, all the while scolding him. “You would do well to remember that every dog on these seas has at some point attempted to lie to me. I know you didn’t do what I told you to, Jack. You haven’t got the balls.”

Jack grabbed handfuls of the sheets before him and cried out in pain. Eleanor was merciless, and he wasn’t sure how much of this he could tolerate.

She went on, “If you had told her, she would most likely have at least returned you with a black eye, but trying to tell me she would be okay with me taking you from her? I wasn’t born yesterday, Jack. I put it together, Jack, and I think I know what you see in her, now.”

She set the strap aside on a nearby nightstand and sat down next to him, pulling him up onto her lap. She continued her work with her bare hand, the sound of the slapping resounding through the chamber. “But you are mine, now. I’ve claimed you, and you are mine. That belt won’t keep her from seeing the bruises this punishment is going to leave, and she’ll know, Jack.”

Jack yelled out, “Why?!” He cried, tears streaming down his face in a sudden torrent, “Neither of you really want me, then, this is between the two of you and has nothing to do with me!”

Eleanor took hold of his hair, turning his face so that they stared into each other’s eyes, “Why didn’t you do what I told you?”

Jack sobbed as his voice broke, “Because I didn’t want to find out how much she cares about me, okay?! I just know, deep down that she would just shrug and tell me to eat her out again. It’s not that she doesn’t care about what you’re doing, it’s that I’m without value to her, and I don’t want to see that…”

Eleanor stopped swatting him a moment, and then started again harder, causing Jack to squirm in her arms, “Didn’t you get it when I said I would take care of you? I know what you need, Jack, and I paid gold to have you away from what Vain did to you. You’re mine, dammit!”

Jack opened his eyes, wiping the tears away enough to see the sincere look on Guthrie’s face. “Wait… what?”

Eleanor smiled at him and stopped her barrage, leaning in close to whisper, “I take care of what’s mine.”

Jack only stared at her in baffled confusion for a few moments, before timidly reaching out to her, cringing even as he did so.

Guthrie felt sorry for this poor soul, who was so scared even to offer such a gesture, so she surprised him again by hugging him tightly to her chest. She whispered only one word as they held each other there, “Mine.”

 

 

 


End file.
